Diethylene Glycol Monomethyl Ether → Ethyl 2,5,8,11,14,17,20,23-octaoxanonacosan-29-oate

HRID 24991

Reaktionsgleichung

Reaktionsgleichung von HRID 24991
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][O:7]CCO.[CH2:11]([O:13][C:14](=[O:42])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37]S(C)(=O)=O)[CH3:12]>C1(C)C=CC=CC=1>[CH2:11]([O:13][C:14](=[O:42])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][O:7][CH2:6][CH2:5][O:4][CH3:3])[CH3:12]

Komponenten

5

Edukt 3

HCID 8134Diethylene Glycol Monomethyl EtherHCID 24758Sodium hydrideHCID 865870276-{2-[2-(2-{2-[2-(2-Methylsulfonylethoxy) ethoxy]ethoxy}-ethoxy)-ethoxy]-ethoxy}-hexanoic acid ethyl ester

Produkt 1

HCID 71366717Ethyl 2,5,8,11,14,17,20,23-octaoxanonacosan-29-oateAusbeute 62,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

NaH (88 mg of a 60% dispersion in oil, 2.2 mmol) was suspended in anhydrous toluene (3 ml) under N2 and chilled to 0° C. Non-polydispersed diethylene glycol monomethyl ether (0.26 ml, 0.26 g, 2.2 mmol) that had been dried via azeotropic distillation with toluene was added. The reaction mixture was allowed to warm to room temperature and stirred for four hours, during which time the cloudy grey suspension became clear and yellow and then turned brown. Mesylate 20 (0.50 g, 1.0 mmol) in 2.5 ml dry toluene was added. After stirring at room temperature over night, the reaction was quenched by the addition of 2 ml of methanol and the resultant solution was filtered through silica gel. The filtrate was concentrated in vacuo and the FAB MS: m/e 499 (M+H), 521 (M+Na). Additional purification by preparatory chromatography (silica gel, 19/3 chloroform/methanol) provided the non-polydispersed product as a clear yellow oil (0.302 g 57%). FAB MS: m/e 527 (M+H), 549 (M+Na).

Aufarbeitung

  1. additionwas added
  2. temperatureto warm to room temperature
  3. stirringAfter stirring at room temperature over night
  4. customthe reaction was quenched by the addition of 2 ml of methanol
  5. filtrationthe resultant solution was filtered through silica gel
  6. concentrationThe filtrate was concentrated in vacuo
  7. customAdditional purification by preparatory chromatography (silica gel, 19/3 chloroform/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-ae90c7b9f46d45c5938d1df1232066fd
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858580B2

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